The 20 most memorable MTV VMA red carpet looks ever

BEST: Lil Kim, 1999

The purple wig, the purple jumpsuit, and the purple pasty are only three reasons Lil Kim has been consistently ahead of the curve in terms of style (and also life). I mean, 16 years later and wigs, jumpsuit, and pasties are all relatively commonplace — especially when looking at the wardrobe of a certain Miley Cyrus (we’ll get to her in a sec).

LEST WE FORGET: Pink, 2000

To answer your question as to what was happening with Pink’s 2000 VMA ensemble, the answer is “everything.” All of it is happening: pink spikes, sunglasses, a crop top, and a fur coat are just a few of the choices made on this infamous night — but yet, they all work. Is it because Pink’s style is notoriously off the cuff? Or because in this one moment she embodies the entire Y2K era? Either way, only Pink.

BEST: Christina Aguilera, Britney Spears, Madonna, 2003

Two brides and a Madonna groom! Two wedding dresses! A cover of “Like a Virgin!” Also, Christina Aguilera had dark hair and nobody talks about it enough.

LEST WE FORGET: Lady Gaga, 2010

The meat dress. The grey wig. The meat hat. This is Peak Gaga™ and therefore amazing — and also un-attemptable by anybody else, so don’t even try.

MAYBE NOT: Lenny Kravitz, 2004

If every search for the definition of “going for it,” please consult Lenny Kravitz’s 2004 VMA outfit in which he tried his hardest to channel the majesty of a Victoria’s Secret Angel…and the mystery of a man who really loves a bootcut jean.

MAYBE NOT: Tyson Ritter, 2009

Glitter is great, but maybe not this much glitter. Or maybe this much glitter, but with a shirt. Or maybe a shirt made of glitter. Just not this.

MAYBE NOT: Jennifer Lopez, 2006

In which Jennifer Lopez looked at her sixties-era gold mini-dress and thought, “Yes, but it won’t be complete without this head wrap.” Or alternately: “I would like to look like I’m going to space.”

BEST: Rihanna, 2012

Not only did Rihanna show up to the VMA red carpet with a pixie cut that would make anybody who’s been told they look good with a pixie cut jealous, but that night she debuted dollar bill nails. As in, she used actual U.S. currency as part of her manicure. Insert every Bitch Better Have My Money joke here.

MAYBE NOT: Katy Perry, 2013

If you’d been waiting your whole life to find out what Katy Perry looks like in grills, you finally got your answer: the way most of us would look. Not great. Not great at all.

MAYBE NOT: Christina Aguilera, 2000

Everybody here is all for self-expression and doing you and every other phrase associated with “you go, girl.” But Christina Aguilera’s very public break from her “Genie in a Bottle” self was bold and busy — but maybe too busy. (That hat or the chains, you know?) Or on the flip side, maybe it’s just too reminiscent of our own aesthetic during that era, in which our paycheques all went to clubbing clothes and self-tanner.

LEST WE FORGET: Katy Perry and Riff Raff, 2014

As if to restore our faith in her fashion choices after the year ‘o grills, Katy perry enlisted Riff Raff to re-live the ultimate Teenage Dream (get it?!): Britney Spears and Justin Timberlake at the 2001 American Music Awards. Genius, inspired, and now only okay if Britney and Justin reunite to recreate it.

WHY (BUT SURE): Miley Cyrus, 2013

Two tiny buns, one (very high) mouse jumpsuit. The inspiration for Halloween costumes and late night talk show jokes everywhere. But let’s face it: she pulled it off.

BEST: Taylor Swift, 2014

Girlfriend used the VMAs an excuse to break — even further — from her squeaky-clean country queen image in a Mary Katrantzou bodysuit, prompting fans the world over to declare with more sincerity than the lyrics from Red: “Don’t you hate pants?!”

ICONIC: Jennifer Lopez, 2000

On the one hand, Jennifer Lopez’s choice to wear a Sean Jean tank top in support of then-boyfriend Sean “Puff Daddy” Combs is great. On the other, she wore a bandana as a handband which is fine, but also a very far cry from the Jennifer Lopez we know today. Who is the real J Lo is what we’re asking. And why does it always come down to hair accessories.

Gwen Stefani, 1998

Were Gwen’s mini buns and blue hair a true reflection of late nineties rebellion? Obviously. (And well done, Gwen!) But less appropriate is/was her affinity for cultural misappropriation. Bindis aren’t just a casual accessory, you guys.

BEST: Britney Spears, 2000

In which she proved (as if she needed to) that she was stronger than yesterday and now it was nothing but her way.

BEST: Beyonce, 2011

It’s true: Beyonce can make even a simple side ponytail land on a “best beauty looks” list. And not only because it was accompanied by the presence of a soon-ish-to-arrive Blue Ivy — mostly because she never wears ponytails so this was nice.

LEST WE FORGET: Lady Gaga, 2011

In her performance of the relatively low-key “You And I,” Mama Monster dressed as her alter-ego, Jo Calderone. His hair is great. And so were the “What’s happening right now?” reactions from various audience members.

BEST: Solange Knowles, 2009

The smokey eye, the frosted pink lips, and a buzzcut with oversize earrings are just another of the million-or-so reasons we should be talking about Solange’s beauty game on a regular basis. Thank you.

BEST: Rose McGowan, 1998

We’ll say it: while Rose McGowan shocked us with her non-existent chain link dress, we’re ready to admit it was bold, brazen, and everything MTV is supposed to be. (See: progressive and controversial.) Do we need to see it again? No, because it’s already been done. Also because this is just how everyone dresses today.